Water → N-(4-chloro-3-(cyanomethyl)-2-fluorophenyl)acetamide

HRID 1430450Notes

Reaction equation

HRID 1430450 reaction equation
CS(O[CH2:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]([NH:14][C:15](=[O:17])[CH3:16])[C:8]=1[F:18])(=O)=O.[C-:19]#[N:20].[Na+].O>CS(C)=O>[Cl:13][C:12]1[CH:11]=[CH:10][C:9]([NH:14][C:15](=[O:17])[CH3:16])=[C:8]([F:18])[C:7]=1[CH2:6][C:19]#[N:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 867136263-Acetamido-6-chloro-2-fluorobenzyl methanesulfonate

Product 1

HCID 86713627N-(4-chloro-3-(cyanomethyl)-2-fluorophenyl)acetamideYield 78.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-acetamido-6-chloro-2-fluorobenzyl methanesulfonate (1.31 g, 3.54 mmol) in DMSO (10 mL) was treated with sodium cyanide (0.868 g, 17.72 mmol), stirred at RT overnight, treated with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-chloro-3-(cyanomethyl)-2-fluorophenyl)acetamide (630 mg, 78% yield) as a yellow solid. MS (ESI) m/z: 227.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-3da25fbead3b4277bd299be922e74606
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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